Just Go With It
by consoul
Summary: "Sam, huh?" he said, practically purring his name. Sam shifted under the sudden intensity of his golden stare, suddenly feeling a bit warm as Gabriel smiled a smile that looked very different from his smirk, but no less dangerous. "I can work with that." Or: Sam gets stood up and is saved by the appearance of a benevolent stranger who is willing to pretend to be his date.


**Just Go with It**

Sam Winchester was in the middle of getting blatantly stood up, and it was largely his fault.

Why he'd agreed in the first place to meet Jess was a complete mystery. Considering all the shit he'd gone through in his relationship with her, he should've _known_ that she would've done something like this to get back at him one more time. How many times had she humiliated or tried to hurt him out of pettiness when they'd been dating? How many times had she been late to dates back when they had been together?

The Winchester shifted uncomfortably in his seat, acutely aware of the knowing, apologetic eyes of the other patrons on him. He'd been waiting for over a half hour now at a clear table for two, and the seat opposite him was glaringly empty. The waiter had already been by twice to see if he wanted to order and had begun to sound pitying the second time. The third time around would probably involve some embarrassing inquiry, and Sam would probably have to skulk out with his tail between his legs.

He bit his lip before picking up his phone, which he'd set on the table in an attempt to stop fiddling with it. He'd already texted Jess and been left on read, which was a pretty clear indicator that she wasn't showing. The fact that she hadn't even bothered to respond after practically begging him for 'one final chance' said it all, and man did it sting. She was probably laughing it up with her friends now at how seamlessly her clever little plan had played out.

Dean's warning words to him when he'd been getting ready earlier came back to him as he stared at the condensation slowly collecting on his water glass.

 _"Just let her go already, Sam. This is obviously some ploy to embarrass you, and you're falling for it hook, line, and fucking sinker!"_

 _Sam eyed his older brother through the mirror. Dean was angry, standing with his burly arms crossed over his chest as he leaned against his bedroom door. He had come straight from the shower when he'd heard what Sam was getting ready to do, and despite the visible suds in his dripping hair and skin, he was still intimidating with his glaring green gaze._

 _"It'll be fine," Sam said dismissively instead of caving to the older Winchester, "Is a tie too much?"_

" _A tie-Sammy, for the love of God, what are you_ thinking _?" Dean asked incredulously._

" _She just wants to talk," Sam said defensively, holding up his two tie options and eyeing them critically. His brother made a rather high-pitched sound of disbelief behind him._

" _Yeah,_ talk _," he said snidely, clearing his throat as Sam arched an eyebrow, "Sam, you shouldn't even have her_ number _, let alone be going to_ talk _to her!"_

" _It'll be fine."_

 _Dean scoffed at his proclamation before shaking his head, anger turning to something more along the lines of disappointment._

 _"Don't say I didn't warn you," he responded ominously, tugging his slipping towel a little higher as he pointed a finger at him, "Even I know this-this_ thing _you and Jess have is toxic, and that's coming from_ me _!"_

 _Sam pressed his lips together and stood a little taller, deigning not to respond as he made a show of fiddling with his shirt buttons. His brother had quickly grown disenchanted with Jess soon after their relationship problems had begun, but Sam was convinced most of it just stemmed from Dean being an overprotective jackass._

 _Behind him, Dean sighed, tsking and shaking his head one more time._

 _"I'll have some beer waiting when you get back," he said gruffly before turning on his heel and departing, leaving a sizeable puddle and his disappointment in his wake._

Sam sighed before tapping his phone against the table. He'd been played for a fool just like Dean had said, and the worst part was that he had only himself to blame. Dean was right; he shouldn't have even had her number in the first place! He should've just deleted it (and maybe received a new one of his own for good measure) and moved on with his life. Instead, he'd kept it, and Jess had wormed her way back into his mind like a parasite.

He knew the whole thing was bad; really, he did. They had had a fairytale start to their relationship, originally bonding over their shared hometown of Lawrence, Kansas. Differing majors in college hadn't kept them apart, and she'd been such a sweetheart that Sam couldn't help but get to know her. Everything had seemed perfect until about six months in when her true colors began to show.

She became demanding and more than a little jealous; always asking him where he was and accusing him of cheating when he was just hanging out with Dean or some friends. Sweet quickly turned sour, and their relationship deteriorated so quickly it still had Sam's head spinning. By what was supposed to have been their one-year anniversary, they had broken up or were _supposed_ to have been at least. Jess liked to string him along over text, or sometimes he'd hear along the grapevine that she wanted him back. She was always there in some way, never really leaving his life.

Sam couldn't help it though. Whenever he thought of Jess, he couldn't help but remember the good times they'd had, and how sweet and lovely she'd been in those early months. It was hard for him to mesh that image of her with the ' _manipulative shrew_ ' (Dean's words, not his) that kept trying to wreak havoc in his life.

After eyeing the empty seat opposite him and then glancing around at the restaurant (and all the whispering, watchful patrons), Sam decided that enough was enough. He wasn't going to keep waiting for Jess like an idiot, and he most certainly _wasn't_ going to let her know how long he had waited for her. The next time the waiter showed up, he'd ask for a check and skedaddle with as much of his dented pride as he could. If he left soon, he might be able to persuade Dean to pull out some stronger liquor tonight and maybe fry up some of his comfort burgers.

 _And then I'll finally listen to Dean and change my number tomorrow, so there's no possible way Jess can reach me._

Just as the waiter began to make his rounds and Sam had scrounged up what remained of his dignity (he was surprised he had any left), a man dressed in what looked like a black silk shirt covered in gold baroque strolled up through the aisle. He was shorter in stature and on the stockier side, with slicked back hair that was either blonde or brown. Sam couldn't tell in the muted, yellow lighting of the restaurant, but if he had to take a guess, it was probably some shade in between.

The shirt was what caught Sam's eye, as it was easily the most striking item in the austere restaurant. In the sea of conservative, normal colors and patterns, the man stood out like a beacon, and as his eyes traveled further, Sam realized his shirt wasn't the only thing that made him stick out.

Maybe it was just the lighting or the gold shimmering on his shirt, but the man's eyes were a captivating shade of amber that, in that instant, looked very bright and yellow.

"I am so, _so_ sorry honey," the golden-eyed stranger said loudly, drawing the attention of the closest patrons as he slid into the seat opposite him. Up close, Sam could spot a very expensive looking gold watch on his wrist and the gleam of a thin, matching chain around his neck, "Traffic was _ridiculous_ today, and you know how panicked the employees get on Saturdays when I leave them. Honestly, they can't even fend for themselves."

Sam blinked as the man leaned in and grasped his hand, lowering his voice as the waiter approached.

"Whoever stood you up is a fucking cunt kiddo. Just go with it, alright?"

The words were accompanied by a wink and reassuring smile before the man leaned back casually and turned to face the waiter.

"Your best merlot to start us off, if you would. Oh, and there's no rush; we have some catching up to do anyway."

With these words, the man intertwined their fingers pointedly, and the alert waiter took the subtle hint as he nodded and backed away without a word.

Sam blinked down at the smaller, tanner hand he was now holding before looking up at the man. His confusion must have been very evident because the man chuckled and patted his hand with his free one before letting go.

"Gabriel Milton, at your service," he said with a grand sweep of his arms. The mischievous and almost roguish smirk that graced his face seemed to be a trademark of his, as Sam didn't think he'd ever see someone make a smirk look quite like _that_ , "It seems like I'm your date tonight, Mr.…"

It took Sam an embarrassingly long moment to realize he was supposed to fill in the blank.

"Oh, uh, Sam. Winchester," he said with a faint flush, "Sam Winchester."

Gabriel waggled his eyebrows, eyes lighting up as he folded his hands together and tucked them under his chin.

" _Sam_ , huh?" he said, practically purring his name.

Sam shifted under the sudden intensity of his golden stare, suddenly feeling a bit warm as Gabriel smiled a smile that looked very different from his smirk, but no less dangerous.

"I can work with that."

Those five words _definitely_ had Sam feeling warm, though he wasn't sure why. Yes, there was a flirty tone to it, but he'd never been attracted to men before. Hell, he could count the amount of one night stands he'd had on one hand, and he hadn't been on a date since he'd broken up with Jess.

Those gold eyes were pulling him in though, and Sam found that he didn't really mind. Gabriel _had_ saved him a lot of humiliation, and who was he to deny help given so freely? The man had put himself out on the line in an attempt to help him, so it was only right that Sam went along with their little charade. After all, things could be far worse.

So, with that, Sam decided to make this as enjoyable of an experience as possible and offered his own edged smile as he responded with, "I'm sure you will."

Gabriel looked taken aback for a second before he beamed.

"I'm liking you more and more, Sam _Winchester_ ," he said, biting his lip for a second before suddenly grabbing his hand, "Waiter's coming up."

They sipped on some wine while Gabriel played with his hand. Sam found that he didn't mind the touch as much as he thought he should've. Maybe if it had been coming from someone less charismatic and charming as Gabriel, but it wasn't, so Sam couldn't find a reason to say anything against it. Gabriel's hand was warm and his fingers deft as they traced idle patterns against his skin and sought out his pulse. It was intimate in a strange sort of way, but also remarkably innocent.

"How old are you, exactly?" Sam asked out of the blue when their wine glasses were emptying. He promptly blushed afterward at his abruptness, but Gabriel only laughed.

"Take a guess kiddo."

Sam squinted slightly at the man, studying his face properly for the first time since Gabriel had sat down.

He was older than him, that was for sure. He had faint crow's feet at the corner of his eyes; enough to show that he smiled a lot and nothing more. The most predominant physical quality he had was gold: amber eyes, naturally tanned skin, golden hair. All of it made for a striking appearance and gave him a more youthful edge that was only accentuated by the baroque on his shirt. Baroque was flashy though, and while Gabriel pulled it off well, Sam didn't think it was a fashion staple of older men.

"Late 20s," Sam mused, trailing his fingers along the stem of his wine glass, "26 or 27?"

Gabriel hummed, a content smile gracing his face, "28. Well done Sam-a-lam."

Sam arched a questioning eyebrow at the nickname, but the man only smiled wider and sipped his wine.

"You, on the other hand, are probably not a day over 21," Gabriel remarked, gesturing to the Winchester with his wine glass, "Couldn't be any younger since we're drinking, but if I hadn't known that I would've said you were 18 or 19. Are you still in school?"

"I start my last year of law school in the fall," Sam confirmed, and Gabriel sat up in interest.

"Oh really? How did you choose to be a lawyer of all things?"

Now feeling much more secure with the situation (it helped that he wasn't being given pitying gazes by the patrons and staff anymore), Sam told all over wine and appetizers. However, instead of keeping it to his usual 'I wanted to help people' explanation, he began with his childhood of all things, telling Gabriel his original desire to prove he could be something more than just a 'Winchester' when he was younger, and that a lawyer seemed like the best way to go at it.

"A 'Winchester'?" the golden-eyed man asked curiously with air quotes, and Sam shrugged.

"Winchesters aren't lawyers, that's for sure," he replied wryly, and Gabriel hummed before gesturing for him to continue.

Tracing his original, half-cocked idea of becoming a lawyer to the ambition that eventually led him to Stanford, Sam told all. It wasn't the wine making him; no, he was barely feeling a buzz from the alcohol. He wasn't really sure what it was, but he thought it was maybe the man sitting across from him listening without a single look of judgment or scorn. If anything, Gabriel seemed engaged and interested, almost as if he were treating this like a real date.

"What a story kiddo!" he exclaimed before Sam could continue down _that_ thought path, "Makes me want to get _my_ life together, and I think I have it pretty neat and tidy. Does your story inspire everyone when you tell it?"

"Well, I usually don't tell it like that," Sam admitted, tugging at his shirt cuff, "I think you're the first person I've ever told that much detail to."

Gabriel looked pleasantly surprised, but before he could say anything, the waiter arrived with their menus.

"I'll cover it, darling," the older man said as Sam flipped through the menu.

The Winchester looked up sharply, and Gabriel pinned him with a pointed look before smiling sweetly.

"This was my idea to begin with, and I was late to boot," he remarked before turning to the waiter and loud whispering, "If I don't cover the check, he'll make me sleep on the couch."

The waiter smiled politely as Sam scowled, blushing fiercely as he placed an order for a chicken and pasta dish.

"Not my fault you can't bother to be on time, _dear_ ," he grumbled, playing on with the charade as Gabriel ordered some medium rare steak.

He could feel Gabriel's eyes on him but kept his gaze on the menu as he sniffed haughtily. Two could play at this game.

"On second thought, I think you should leave the bottle," Gabriel quipped with a sigh, "It seems I'm in the doghouse already."

Someone at a neighboring table snickered, and the waiter refilled their wine glasses before collecting their menus.

"Who really stood you up, Sammy?" Gabriel asked as he leaned in, so they wouldn't be overheard. With him came the smell of the merlot they were drinking and the subtle scent of spicy cologne, and Sam found himself leaning just a fraction to match instead of protesting the second (or third?) nickname he'd been given.

"It's…a long story, Gabriel," he muttered, watching as the man's amber irises flicked down to his lips. Was the man really interested in him?

Gabriel propped his chin in one hand before reaching out with the other to sweep of strand off his cheek, warm fingers brushing along his skin in a faint caress that ended just as soon as it was started.

"I have plenty of time," he responded, his breath fanning across his face in a warm and sweet arc, "And call me Gabe."

Sam stared at him for a moment, debating whether or not he should tell Gabriel- _Gabe_ , about the mess he'd gotten himself into with Jess. The man's hand drifted down to his shirt collar, smoothing what Sam knew didn't need to be smoothed out.

 _What's the harm in telling him? He hasn't judged you at all at any point in this little charade of ours, so why would he now?_

"All right, _Gabe_ ," Sam said with a bit of a smirk before pulling away (close proximity to Gabe was a _very_ bad idea), "Jess is the 'fucking cunt' that stood me up, but this hasn't been my first rodeo run with her."

"Why do I get the sense I'm going to hate this Jess character even more than I already do?"

"You probably will. My brother despises her," Sam remarked before scratching his neck, "I know this is all going to sound really bad and make me look pathetic, but in the beginning, everything was good…"

Telling Gabriel about Jess was…less awkward then he'd expected. There were moments where Sam stumbled over his words because there were points where he really wasn't sure _how_ to explain to Gabe the tumultuous relationship he'd had with her without making himself look like a dumbass, but the further he progressed and talked things through, he realized two things.

Exhibit A: He had been a dumbass when he came to Jess. Sure, their relationship falling apart wasn't on him, but everything after what was _supposed_ to be a clean break up was. He'd let himself get caught up in her antics when in reality he should've stayed well away from her. There was no way to sugarcoat it.

Exhibit B: Gabe wasn't judging him for _being_ a dumbass. There was definitely disappointment at how he handled recent things with Jess (texting her post-breakup had earned him an aggrieved sigh), but Gabe didn't seem disgusted or frustrated with his relationship idiocy.

"…and that's how I got here, sitting at this table like a moron." He finished, sighing as he slumped back in this seat, "You know, putting it out there like that made me really realize how dumb I've been."

"Talking things out tends to do that," Gabe said sagely before his eyes slid over to some point behind him and he smiled, "But now the lady taking pictures of us from the bar makes a lot more sense."

Sam stiffened, and the older man tutted before grabbing his hand, his seemingly innocent looking grip masking the real strength he was gripping him with.

"Ah, ah, we can't let her know she's been caught out," he murmured, "I have the beginnings of a plan brewing, but it all depends on if you want revenge against Jess or not."

"What do you mean?" Sam asked, and Gabe pinned him with a searching look.

"You're a good kid, with a big heart," he said bluntly, a small smile gracing his face, "And there's nothing wrong with that, but you might not want to get revenge against your ex because of it."

His face was different; more serious and harder. Gone was the joking, extroverted stranger that had put him at ease with his winks and listening ear. Sam was catching a glimpse of what he thought was a very important facet of Gabe's personality, and while it was intimidating as hell to see the pint-sized guy look so dead set on dishing out karma, it wasn't scary. If anything, it just made Sam curious to see what the man was capable of. He was well aware that throughout the course of the evening Gabe had revealed next to nothing about himself, and maybe this was an opportunity to learn something about him.

Why Sam wanted to know so bad, he didn't know, but it wasn't every day that something like this happened to him, and for once Sam just wanted to see where the chips fell. Besides, tonight had been the last straw when it came to Jess, and he wasn't feeling too charitable towards her anymore. She deserved some comeuppance.

"Don't let me stop you from having a good time," Sam replied, and Gabe arched an eyebrow before smirking devilishly, eyes gleaming with satisfaction.

"Oh, this is going to be _fun_ ," he said, sounding truly eager, "Now, do you happen to know any leggy redheads?"

Sam bit his lip, frowning momentarily before scoffing in disbelief and pulling out his phone, quickly opening his Instagram and pulling up a picture.

"This her?" he asked, showing him the picture, and Gabe nodded.

"Yup. She's wearing a LBD with some obnoxiously scuffed up pumps at the bar, and she's taking pictures with her phone."

"Then we're dealing with Anna, one of Jess' close friends," Sam said distastefully as he sipped some wine, "She comes off as holier than thou, but she doesn't get her roughed up knees from praying, that's for sure."

Gabe roared with laughter, the hearty sound drawing the attention of several patrons as he just _laughed_. It startled Sam enough that he nearly dropped his wineglass before he processed what he'd just said and blushed slightly, ducking his head to hide behind his hair as Gabe reached for the wine bottle.

"You're a little spitfire, aren't you?" he asked as he poured himself a healthy serving of wine, " _God_ , this evening just keeps getting better and better."

Sam blushed harder as Gabe grinned and toasted him with his glass.

 _He's kind of hot when he grins like that._

Luckily the waiter showed up with their meals before Sam could embarrass himself any further, and the two men tucked into their meals with an appetite reserved for those with an eagerness for the activities to come after the meal.

"So, before you explain your ingenious plan to get back at my ex," the Winchester began, pointedly using the term 'ex' instead of 'Jess' (it was a start at least), "Do you mind if I learned a little more about you besides your name and the fact that you like gold?"

Gabe looked up from his steak before shrugging and gesturing with his silverware for him to continue.

"Ask whatever you want. This _is_ a date after all."

Sam ignored the man's flirtatious smile in lieu of asking the questions that he'd been meaning to ask ever since Gabe had sat down.

"What's your career? You're dressed pretty flamboyantly, but it suits you so don't take offense," Sam added hurriedly, "And why are you snickering at me now?"

Gabe was trying to hide his laughter behind his wineglass, but the man quickly gave up pretenses, waving a hand as he took a deep breath.

"Oh, I'm sorry kiddo, it's just that I don't think I've met someone that hasn't had an inkling of what I do."

"Wait-are you famous or something?" Sam hissed furtively as he leaned in, his mind racing with the possibilities. What was Gabe even famous _for_ , and if he was, would they end up in the tabloids or something? This could throw a major wrench in their revenge plans; Sam just wanted to get back at Jess, not end up entangled in some sordid celebrity news!

 _Me, wining and dining with a celebrity? It's the end of the world!_

Gabe shrugged lackadaisically, "Something like that. Ever heard of a nightclub called the Fallen Angel?"

Sam's eyes widened, "No way. Do you-"

"I do," Gabe confirmed, "Say hello to the owner of the most exclusive nightclub in the city."

If Sam was a less intelligent person, he would've let his jaw drop to hit the table. He was incredibly tempted to gape like an idiot but managed to control himself as he scrambled for something to say.

"What-wait, you're the _Trickster_?"

"In the flesh," Gabe said with a winsome smile, and Sam stared before grabbing his water glass and chugging it.

"I've had too much wine, and I'm imagining things," he muttered, feeling himself going into a state of shock just _considering_ the idea that he was sitting across from _the_ infamous Trickster.

The Trickster was a celebrity infamous for putting Lawrence on the map. His nightclub had drawn in so much business that people didn't really care that it had been a _nightclub_ that had breathed life back into the city. Despite his social media and constant presence in the Fallen Angel, little was actually known about him. There were so many rumors surrounding him that it was hard to separate the grandiose myth from the actual man.

"Nope, I'm very real," Gabe, no, the _Trickster_ , quipped, "If you want, after we exact revenge, we can go back to the Fallen Angel?"

"No, I can't-wait, for real?" Sam asked in disbelief, "That place is like-like the playground for the gods or something. I'd have to kill someone just to be able to stand in line to get in!"

"Well, tonight's your lucky night," Gabe said cheekily, "But enough about _boring_ little me. Let's delve into how we're going to get back at your bitch of an ex!"

Sam thought 'boring' was the absolute wrong adjective to describe Gabe but continued on reluctantly.

"What _are_ we going to do?" he asked suspiciously.

"Well, take things up a notch if it's ok with you," Gabe responded as if it was the most obvious thing in the world, "There are two things we can do here. Plan A is we can continue to act lovey-dovey before we head back to the Fallen Angel, where I will make a tell-all Instagram post exposing you as my 'secret lover'. Plan B is that we leave, but confront Anna outside, because I'm pretty sure she's not taking pictures for just Jess to look at."

At the second part, Gabe seemed truly sympathetic as he looked at him with soft eyes, and Sam froze as he processed the implications.

"You don't think…actually no, I wouldn't put it past her," he said with a bitter laugh. Gabe probably got hounded by paparazzi and fake people all the time, so who better to speak on the subject than him? "Can you pull up Instagram? I have her blocked."

Gabe handed over his phone without a word, but Sam could see him glaring over in Anna's direction as he pulled up Instagram and quickly searched up Jess.

The most recent post was a picture of him posted about half an hour ago of him talking to the waiter. The caption was short and to the point, but it still turned Sam's stomach as he read it.

 _Set up my ex for laughs The Jewel. Like I'd ever get back with his boring ass rofl._

There was one comment beneath the picture, and Sam pulled it up automatically, dreading what it said.

He recognized the username immediately and chuckled incredulously as he read the comment.

"You ok Sam?" Gabe asked in concern, and the Winchester shook his head, unable to vocalize what he was feeling at the moment.

"It's just Charlie. One of my brother's friend isn't very pleased with Jess," he said, handing Gabe back his phone to let him read what Charlie had written.

 _blondiejess: You just crossed a line. How can you be so cruel? Dean's going to come for your ass, but not before I do!_

Gabe chuckled before looking at the post, where his face instantly darkened. It was a jarring shift, and Sam suddenly felt uneasy as the man's smooth, unreadable face took in the post.

"Who's Dean?" he asked, his forced attempt at a pleasant tone only adding to the sudden nervousness Sam felt.

"Uh, my older brother. He hates Jess," he replied, and Gabe hummed noncommittally.

"Then he's a smart guy," he said distractedly, "Sam, I don't want to force you to do anything you don't want to, but right now I'd really, _really_ like to go with Plan A and give the bitch a taste of her own medicine."

Jess had genuinely pissed him off; Sam could tell by Gabe's tone of voice and the tenseness in his jaw, and he didn't blame him. Sam himself was pretty pissed off (and a little hurt too) over how cruel she'd been, but what he didn't understand was why Gabe was taking it so personally. They had only met an hour ago for Christ's sake!

"You really want to help me get back at her?" he asked, and Gabe nodded gravely.

Sam looked into the man's anger darkened eyes, only seeing genuine anticipation over what decision he'd make, and a strange amount of concern.

 _He really cares about this. And maybe a little about me too._

"Then we're going Plan A all the way," he proclaimed, his anger fueling his determination.

Gabe smiled wolfishly before grasping his hand and planting a cheeky kiss of triumph on the back of it. His lips were warm and soft, eyes alight with mischief and glee at Sam's choice.

"Plan A it is," he said as Sam blushed, "Your ex won't know what hit her."

…

Sam Winchester did, despite all accusations, know how to have fun. He just didn't have so much of it due to the high value he placed on his education and learning in general. If he had to choose between a house party and a book, he'd probably go with the book after a few minutes of thought, but if someone cajoled him enough (and if he was in the partying mood, which did happen occasionally despite popular belief), he was just as likely to go to the party.

Which was why he wasn't completely out of his element when Gabe suggested they ditch the restaurant and make their way back to his infamous nightclub, so they could enact Plan A to its fullest effect. In fact, he was even looking forward to it, if only so he could have the bragging right that he actually set foot in the place. The Fallen Angel was for Lawrence what Mount Olympus was for the Greeks; lofty and accessible only to the gods.

What he _wasn't_ prepared for was the Lamborghini parked against the curb, all sleek lines and glossy black paint. Compared the rest of the normal cars in the area, it stood out like a whopping sore thumb, and Sam could only gape as Gabe led him to it.

"Is this _yours_?" he asked dumbly, and Gabe shrugged, cocking a hip as he eyed the car critically.

"Technically it's Balthazar's," he responded before explaining further as he caught the confused look on Sam's face, "My cousin and liquor supplier."

"I see," Sam said for lack of any other response as Gabe stepped forward to lean with his back against the car. A casual motion many people with cars did, but with the way Gabe was dressed, and against a _Lamborghini_ of all things, it painted a much different picture with its overtone of wealth.

Gabe clucked his tongue before reaching out to punch his shoulder playfully, apparently trying to ease the newfound tension.

"What's the matter, kiddo? Afraid you won't fit?" he asked with a roguish smile and exaggerated once over of the Winchester's body.

Sam chuckled nervously, eyes still stuck to the car as expensive as his college tuition, "Yeah, uh, that's one problem I guess."

Gabe raised a questioning eyebrow before his expression changed as he looked past Sam, who was already feeling a sense of déjà vu.

"Again?" he groaned quietly as the man clasped his hand smoothly and tugged him forward. Gabe leaned back against the car, and suddenly Sam was towering over him, their hands linked casually.

"Act natural," the older man whispered before reaching out and tugging at Sam's belt loop with his free hand, getting the Winchester to the very edge of the curb and that much closer to him.

Sam tilted his head as Gabe's hand lingered at his hip. He could hear the clack of heels approaching and made a split-second decision.

With his heart in his throat, he bent down to whisper by Gabe's ear, lips brushing the spot just below the man's earlobe. He wasn't sure what he had intended by the action beyond selling the act a little more convincingly (to an outside viewer, their status as a couple couldn't have been questioned with an action like this), but as Gabe's hand tightened on his hip, Sam suddenly found words to say.

"Is this _natural_ enough for you, Trickster?" he murmured, drawing a minute shiver that he could only enjoy for a second before he straightened back up, an innocent expression plastered on his face to hide the fact that he had _enjoyed_ doing all of that.

"Sam! Sam, what are you doing?"

The Winchester turned, doing his best to act completely surprised by Anna's appearance. To his amusement, her pumps _were_ pretty scuffed up as Gabe had said, and she appeared to be a little tipsy. Probably from all those drinks she'd had at the bar while she'd been spying on him, the little bitch.

 _Reign it in, Winchester. They'll get their just desserts soon._

"Oh, hey Anna!" he exclaimed, smiling genially as the redhead's gaze became entranced by the Lamborghini.

"Friend of yours, _darling_?" Gabe asked casually. His eyes remained fixed on Sam though, golden irises captivating as he ran an elegant hand through his hair to ruffle it.

 _Cheeky bastard,_ Sam thought, taking it all in, and Gabe smirked slightly as if he knew exactly what was running through Sam's mind.

"Wait- _darling_?" Anna spluttered, eyes wide as she tore herself from her Lamborghini-induced trance.

"She's one of Jess' friends. Haven't seen her in a while though, " Sam explained, "We really should get going if we're going to make it on time Gabe."

Anna almost gave herself a case of whiplash looking between the two of them, she was that confused.

"But-Sam, I-weren't you supposed to meet Jess- "

"I honestly don't know what you're talking about," Sam interrupted smoothly, "I haven't seen Jess in quite a bit though, and you _are_ interrupting my date night, Anna."

The sense of righteous vindication that filled Sam as Anna's face turned to one of utter shock almost had him wanting to either bust out laughing or ask her what the _hell_ did she think she was doing right then on the spot, but luckily Gabe swooped in before anything disastrous could happen.

"It was nice to meet you, but we really _must_ go," the older man remarked, rubbing his thumb soothingly into Sam's hand, reminding the Winchester that they were _still_ holding hands, "The club gets _so_ busy on Saturday nights, and neither of us likes to idle at such… _pedestrian_ establishments when we can have fun at _my_ place."

With an arrogant grin that went right with his haughty words, Gabe pretty much dismissed Anna as insignificant, and all three of them knew it.

An angry flush began to crawl up the redhead's cheeks as she realized what had happened, but Gabe was already opening the passenger door for Sam and walking around to the driver's side, a few final words addressed to Sam, but spoken in a pointed enough tone that Sam knew Anna was meant to hear.

"Hopefully we haven't lost too much time, honey. The Fallen Angel is _so_ hard to get to when traffic gets backed up."

Sam didn't think he'd ever forget the sequence of Anna's expressions as she processed the information. Through the window of the Lamborghini, he could just manage to see her embarrassed and angry face turn to brief confusion, and the utter stupefaction as she realized that Gabe was _the Trickster_ and that _Sam Winchester_ was supposedly _dating_ one of the most elusive, elitist members of Lawrence.

The throaty, smooth roar of the Lamborghini as Gabe pulled away from the curb couldn't manage to drown out the sound of Sam's laughter as they sped away.

"Holy shit that was _great_! But 'pedestrian establishments?'" he asked between chuckles.

Gabe had the grace to look sheepish for a moment before he tossed his head in a faux manner of arrogance to save face.

"Hey, The Jewel is like a solid 6/10 at best, but definitely _not_ my kind of place. Way too bland."

Sam turned in his seat (which was very plush and supple; Dean would _kill_ to be in his position), one of the questions he'd kept simmering on the back burner coming to the forefront with his curiosity.

"So what _were_ you doing there in the first place?"

Gabe glanced over at him, golden irises aflame with the burning combination of the summer sunset and the streetlights coming on as a result.

"I drop by different places in Lawrence both because I like to switch things up and to keep the paparazzi off my tail. A set routine is just asking for trouble, so I make it a habit to bounce around. I ran into a couple of them a few blocks over when I was coming out of the bank, so I picked the first place that stood out to me when I was getting away. It just so happened to be The Jewel."

A meeting of pure chance. Sam couldn't say he was surprised; he too had gotten the sense The Jewel wasn't exactly Gabe's sort of place, but it still seemed odd to think that meeting the infamous Trickster had come down to a simple case of auspicious timing.

"Well, I'm glad I met you," the Winchester said genuinely, "It's been a while since I've taken a good step out of my comfort zone."

Gabe stared at him for a moment before grinning happily, clearly returning the sentiment.

"You mentioned you go to Stanford," the man said after a few moments of silence, "Do you always come back for the summer?"

"Yup," Sam replied, "I used to stay with my parents, but now I stay with Dean…"

The Winchester frowned, something occurring to him that had him abruptly switching subjects.

"Wait, how did you know Anna was there for _me_?" he asked, confused, "If you get followed by paparazzi all the time, then why didn't you assume she was just one of them?"

"Good question, Samantha," he said, ignoring Sam's scowl at the newest nickname, "And the answer relies on a few things. For one, she wasn't doing a very good job of being covert at all. Two was that she was using her phone, and while some paparazzi rely on them when they need to be extra sneaky, a lot of them prefer cameras for quality. The third, and final reason was that I noticed she was there _before_ I walked in and was more focused on you than me."

Sam nodded, thinking over what he'd been told.

"That's pretty clever of you," he commented, "No wonder you managed to make the Fallen Angel the hottest party spot in Kansas."

Gabe smiled cunningly, but Sam noted the faint blush at his praise with amusement.

The drive to the Fallen Angel was a wild experience in itself for Sam. Between the luxury vehicle he still couldn't _quite_ believe he was actually sitting in, to the abrupt halts that typical Lawrence traffic brought, the theoretically fifteen-minute drive to the club ended up being easily double that. Sam watched the sunset in a conflagration of oranges and reds while Gabe turned up some music and honked his horn more than Sam had ever seen anyone use their horn.

"Impatient much?" he teased as Gabe laid on the horn _again_.

"A little, but you'd be too if you were trying to get to _this_ ," he said, whipping the Lamborghini around the last corner to finally reveal the Fallen Angel.

Sam had never seen the club in person despite his lifetime residency and subsequent intimate knowledge of Lawrence. He'd seen pictures on social media of the place though, both inside and out, and knew it was an outrageously wild, yet elegant place where someone was guaranteed to have a good time. Pictures, however, simply didn't do the place justice.

The line that wrapped around the corner they'd just turned distracted the Winchester for a moment (people really _did_ line up to get into the place), but not for long. Lights drew his attention towards the sleek, four-story building sitting at the end of the street, dominating the corner with its lit up golden and white lights. A sign in glowing cursive read 'Fallen Angel' above a set of spread neon wings placed above the entrance, which seemed to be heavily guarded by bouncers dressed in black.

"Like it?" Gabe asked as they cruised down the street towards the entrance, and Sam nodded dumbly, already a bit overwhelmed by it all. He noticed that only the first floor and the top had windows; the second and third were just walls.

"Is the fourth-floor special?" Sam asked as Gabe pulled up to the curb. People were already craning their necks to look at them curiously, but luckily the windows were tinted enough that they had a modicum of privacy.

"Fourth is my apartment," the man explained distractedly as he unbuckled his seatbelt, "All right, lemme see you."

Sam turned towards Gabe curiously, who cast a critical eye over him before reaching over to make what seemed to be nightclub attire adjustments.

"Attire for my club is on the more cleaned upside, but not _this_ cleaned up," Gabe said as he undid the top button of Sam's button down and ran a hand through his hair. Sam held still obediently, even as the man's hand slid down to brush his jaw.

"Anything else I should know? How _are_ we going to pull off Plan A?" he asked, suddenly hit by a bout of nerves. How on Earth had he ended up outside of the Fallen Angel with the Trickster in his Lamborghini?

 _Well, technically it's his cousin's, isn't it?_

"To be honest, probably getting out of the car with you will do," Gabe admitted, "I don't really show up to the club with lovers so…publicly like this. I always smuggle them in to avoid gossip as much as possible."

The thought of Gabe partying the night away with someone else made the pit of Sam's stomach burn. The feeling was quickly identifiable, much to his profound horror. Jealousy over who Gabe chose to spend his time with was ridiculous; the man was handsome and had a reputation to boot, so it made sense that he'd have people throwing themselves at his feet. And yet…

"If I'm going to get revenge against Jess by pretending to be with you, then I better do it the best way possible," Sam said firmly, ignoring the slight pang he felt as he said 'pretending'.

Gabe gazed at him for a moment before nodding, a sudden shift overtaking his features. A smug smirk and mischievous glint replaced what Sam realized had been thoughtfulness, turning Gabe into the Trickster in the blink of an eye.

"Then let's do this," he said, gesturing for him to wait as he got out.

The increase in volume as Gabe stepped out was noticeable and only grew as the man strode around the front of the Lamborghini. It was clear that he had company tonight, and Sam mentally prepared himself for what was probably going to be one of the wildest nights of his life as Gabe opened his door.

"I hope you know what you're doing," Sam whispered as Gabe took his hand to pull him out, and the older man smiled reassuringly, the softer expression a brief flit across his face.

"Don't worry. I've got you," he said quietly as the crowd quieted a bit.

Sam nodded shallowly, trusting in the man (and what a wild thought that was: trusting the Trickster) as Gabe snaked a loose arm around his waist and turned him to face the club.

Cameras flashed as people shouted, wanting to see who Gabe-the Trickster- had decided to bring. It nearly had Sam wanting to dive back into the safety of the Lamborghini, but Gabe kept him on track with his arm as they walked towards the club.

"Just keep your eyes on the door, kiddo," Gabe muttered as the people in the front of the queue automatically parted to let them through. There seemed to be hundreds of eyes fixed on Sam, who decided that sticking as close as humanly possible to Gabe would be his best bet at success.

Sam's plan only solidified further as they entered the nightclub. It was fancier than any nightclub he'd ever visited despite the typical flashing strobe lights and dance music. There was an undercurrent of wealth to it that could be spotted in the clothes and beautiful people and fancy drinks. Nightclubs also weren't in the habit of using dark hardwood floors and marble counters edged with gold; at least none that Sam had ever been to.

"What do you think?" Gabe asked as they strode in deeper. The floor they were on was edged with a catwalk that ran the entire length of the room some ten feet above their heads, exposing patrons looking down from tiny personal tables. The dance floor in front of them was recessed into the floor a few steps to separate it from the counters and was made even more distinguishable by what looked like inset lights around the whole floor.

"I don't even know where to begin," Sam said over the bass thrumming throughout the whole building. It even _smelled_ expensive, and he realized that the Fallen Angel reflected its owner very well.

"Is that good or bad?" Gabe asked, and the Winchester looked down to see that the older man looked a bit nervous.

 _Does my opinion matter that much to him?_

"Good," Sam said after a moment, liking the way the dim lighting made Gabe's eyes stand out, "It looks like you."

Gabe tilted his head, a questioning look appearing in his eyes.

"And what do I look like to you?"

They were standing at the edge of the dance floor, bass vibrating through their heels and forcing Sam closer so Gabe could hear his response. Sam wasn't in the habit of being very bold when it came to flirting, but stranger things had happened in the course of the evening, and he didn't feel awkward at all about his forward advances when it came to Gabe. Maybe it was because the man himself was so brash, or because he thought he could feel something developing between them as they played this revenge game.

 _Or maybe this is all a weird dream and I'll wake up at my desk surrounded by energy drinks like I usually do._

Sam knew that this wasn't a dream, however fantastical and surreal the whole situation had become. Gabe was _real_ , from his slicked-back hair and spicy scent to his baroque shirt and dangerous smirk. The nightclub only added an element to the already mysterious man; an allure of power and prestige that only lured Sam in even deeper.

Maybe it was a bad idea getting caught up in Gabe; Dean would certainly say so. But Dean wasn't here, and Sam _liked_ the game that they were playing. Their little revenge plan was working, and Sam found that he rather liked how being bold had worked out for him so far. What was one more step outside his comfort zone?

 _It can't be that bad if it's just one more step closer to Gabe._

"It looks beautiful," Sam murmured into the man's ear, his hand brushing Gabe's elbow as he bent down to say the three words before drawing back slightly.

Gabe's smirk had slid away to reveal a much different face. It looked closer to shock, but Sam swore he could see a flush on his cheeks.

Before the Winchester could read the older man's expression any better, a man with a half-unbuttoned silk shirt and the tightest leather pants Sam had ever seen in life strolled up with a phone brandished like a weapon in his hand.

"Gabriel Milton, _please_ tell me why I'm seeing pictures of you already trending with a- oh my, who is _this_?"

The man tilted his head and arched an eyebrow questioningly as Gabe turned, his Trickster face firmly back in place much to Sam's disappointment.

"Oh, it's part of a revenge plan," the man replied blasely, though Sam thought there was still a bit of pink lingering in his cheeks (or maybe it was the lighting playing tricks on him), "Balthie, this is Sam; Sam, this is my cousin Balthazar."

"Hello, _Sam_ ," Balthazar purred, somehow fitting his phone into his pants pocket.

"Uh, hi," Sam managed to say back, and Gabe rolled his eyes before shoving Balthazar a bit.

"He's my man for the night, cuz, but _you_ will be my wingman."

"Wingman?" Balthazar asked, looking quite affronted, but Gabe was quick to sooth as his expression turned playful.

"I'm going to need you to put that photography major to use."

The two of them gazed at each other for a second, and Sam watched with fascination as the two clearly had a whole conversation, complete with debate, with just their eyes. He and Dean had done something similar before on occasion, but he'd never really seen anyone else do it with this intensity.

 _Now I get why people think it's creepy when Dean and I do it._

Their simultaneous grins sent a shiver down Sam's spine, and Balthazar was the first to turn away as he looked at him with a new mindset.

"Revenge, huh?" the man asked, clearly interested to get in on the plan, "I'm _so_ in. Tonight is your lucky night Sam."

"Do I want to know?" Sam asked as he was shepherded towards what looked like the main bar. There was an impressive display of alcohol in all sorts of bottles lined up on glass shelves that stretched up and up, and he got the distinct feeling that once someone sat at that bar, they weren't going to walk away sober.

"Don't worry, you'll be in good hands," Gabe commented, and Balthazar grinned in response.

" _Very_ good hands. But first, we need drinks!"

…

And so they began with drinks. Of course, just one wouldn't do at all, and Balthazar seemed to be a master at coming up with the most brilliant concoctions of alcohol. Everything Sam drank was either sweet or burned like fire, and all it led to a very, _very_ drunk Winchester by the time the party really got started.

It was an odd state for Sam, who hardly ever got truly drunk. His alcohol tolerance was just too high, and he wasn't a big drinker anyway save for beer with Dean, and beer wasn't much. Hard liquors and cocktails were _much_ different though, but the more Sam drank, the less he cared. It was hard to when he was easily having the night of his life.

Gabe stuck close to him as they drank and chatted to random people that came up to greet the infamous Trickster. A lot of them were equally interested in Sam, much to his shock, and Gabe was quick to introduce them as 'lovers', his hands always roaming some part of him as he praised him to the high heavens.

"He's studying to be a _lawyer_ -I know, he's just so _smart_ …"

"Oh, I think he works out; aren't I right, honey? Definitely with _these_ shoulders…"

"Isn't he gorgeous? Sam just has it all, doesn't he?"

Sam certainly felt like he did. If Gabe inflated his ego anymore, he was going to float away towards the shadowed catwalks above. His face had a permanent flush to it, born from a combination of drinking, Gabe's compliments, and the man's ever-present touch. His hands were brushing his shoulders, running along his thigh or arm, and even running through the ends of his hair. The first time the man had brushed his lips along his cheek, Sam thought he would spontaneously combust, but had managed to hide his shock with a shot of some very nice tequila.

Gabe wasn't the only one being handsy though. Alcohol had the magical tendency to loosen inhibitions, and Sam was no exception, growing bolder as he got drunker. Gabe looked more and more alluring as the night progressed, somehow managing to perfectly chat up everyone that came their way despite the fact he'd been having even more to drink than him. His flawless performance under pressure made Sam admire him all the more, and so he let his hands roam in return.

"How're you feeling, kiddo?" the older man asked once interest in them had ebbed a bit. Dancing on the floor had grown with the appearance of some celebrity Sam didn't know well and didn't care to know when the most elusive man in Lawrence was sitting beside him with a cheeky smile.

"I'm feeling great," Sam slurred as he let his hand run across the raised baroque pattern of Gabe's shirt. He was pretty sure his own smile was dopier than he'd like, but the Trickster didn't seem to mind as he leaned in to grip Sam's collar.

"Feel like taking this to another level?"

The question sobered Sam up a bit, but he didn't move from the close proximity their faces suddenly held.

"And what would that entail?" he asked (he couldn't be _that_ drunk if he could use 'entail' correctly), earning a more serious look from Gabe.

"You have to find out," the man responded, gold eyes flicking down to his lips.

Sam was sure he hadn't imagined that or the slight tilt of Gabe's head, but he still found himself hesitating. What if he had read the signs wrong, if there were any signs at all?

 _Oh, come on. The guy saved your ass from a humiliating stand up from Jess, drove you to his personal nightclub, and introduced you as his lover to half of Lawrence's elite just so you could get some revenge. And he did this all while flirting heavily with you._

The voice (which was decidedly irked sounding) had some good points, but Sam wasn't a one-night stand guy, even if he was roaring drunk. He, much to his embarrassment, had grown attached to Gabe. He truly liked the man and didn't want tonight to be the only night he had with him.

 _Yeah, well it's about to get cut short if you don't hurry up and make out with him._

Sam made a frustrated little noise in his throat before deciding to throw caution into the wind and go for it. He'd already done it enough time tonight that he could put himself out there one more time.

Before what was left of his rational mind talked him out of it, Sam closed the scant inches left between them and kissed Gabe.

He hadn't kissed anyone in a while and hadn't _ever_ kissed a man, but Sam _knew_ this wasn't just some random, drunken kiss. It felt _right_ , from the warm spike of excitement running down his spine to the way Gabe readily kissed back. Sam wasn't sure what was louder: the thrumming bass or his pounding heart, but Gabe was eager and fighting for control, and Sam wasn't willing to give in so easily.

Gabe's lips were just as warm as the rest of him, and Sam pressed forward more intently, grabbing the man's collar and tilting his head for better access as Gabe sighed into the kiss and gripped the front of his shirt in return. Sam's fingers brushed against the gold chain he'd noticed earlier that night, and the metal was like a brand compared to the heat of the kiss.

Sam was vaguely aware that they were drawing attention if the increase in voices was any indication, but he didn't really care as he gripped Gabe's jaw and let his fingers slide back to tug at the curled hair along the nape of his neck. He tugged hard enough to make the man gasp a bit and took the opportunity to bite Gabe's lower lip before drawing back for breath.

The man looked as if he'd enjoyed it, which was _very_ good. He wasn't saying anything though, which was very _bad_. Balthazar was squealing about getting the perfect picture from behind the bar, but Sam couldn't make much out over the sudden nervous feeling that overtook him.

 _Fuck, what was I thinking? That's the last time I listen to alcohol-induced voices in my head!_

A breathless chuckle drew Sam out of his spiraling thought process, but he still jolted in surprise when Gabe leaned forward to latch his mouth on his neck.

"Oh wow," Sam said intelligently as the man boldly licked a stripe over his skin.

Gabe's laugh vibrated through the Winchester's skin, his deft hand curling around Sam's wrist as he nibbled lightly.

"Wow indeed," he replied with a much huskier voice as he pulled back, "I've been wanting to taste you all night."

 _That_ sent a much different spike of heat running down his spine, and Sam leaned forward hungrily. The words were confirmation that he got at least tonight with the Trickster, and he wasn't going to waste what few hours he had left.

Gabe pulled back though, causing Sam to groan in frustration as the tantalizing skin of Gabe's neck was taken away.

" _Now_ you want to be a tease?" he asked, but Gabe only winked and tugged him off his barstool.

"Send me the pictures, Balthie," he called to his enthusiastic cousin, who waved in response, "Come on Sam. Don't you want to see the top floor?"

"Fuck yeah," Sam responded as the room swayed around him. He managed to keep his stride relatively straight though as Gabe led him away from the dance floor and music to a barely noticeable door tucked away from all the activity. Gabe pulled out a keycard and swiped it to open the door, earning an impressed grunt from Sam.

"Fancy," he drawled, and Gabe laughed as Sam's eyes lingered on the keypad.

"That's not the fanciest thing I have to offer."

Sam perked up as they walked down the hall towards a set of elevator doors, grinning like a little kid as Gabe swiped his keyboard once more to reveal mirrored walls and a matching ceiling. In his drunk state, all the duplicates of them seemed to sway and dance in his mind.

"So, this leads up to your…lair?" he asked as the doors slid shut smoothly.

"Lair? How drunk are you, Sam?" Gabe asked, and the Winchester shrugged, pushing Gabe back against the wall and pressing his lips to that spot just under his ear, his hands sliding down to grip his hips.

"Uh, very, but in my defense, only people with lairs have elevators that lead _up_ to them," he mumbled against Gabe's neck, enjoying the scent of his skin enough to delay sucking on it.

Gabe pushed him back before he could though. It was a gentle push, but in Sam's drunken state, it was enough to make everything spin as he teetered dangerously on suddenly weak legs.

"Oh boy," he said, tilting to the left, and Gabe cursed before tugging him upright, holding onto him as Sam took a long moment to regain his balance.

"'Very' is an understatement," he said as Sam became fascinated once more by their multiple reflections, "You don't drink often, do you?"

"Nope," Sam replied, alcohol making him blatantly honest, "You smell nice."

"I know," Gabe said with amusement as the elevator doors dinged open, "C'mon kiddo. Let's get you horizontal before you do something dumb."

Sam followed Gabe out of the elevator and into the biggest living room he'd ever seen. Like the dance floor downstairs, it was recessed into the ground, and the couple of steps gave him some trouble as Gabe attempted to lead him to the leather furniture arranged in a U to face the large TV mounted on the wall. Unlike downstairs, the dominant color seemed to be white, but gold and black accents made it easily recognizable.

"Oops," Sam said as he tripped on the edge of a rug, falling half onto the nearest couch with a thud that he had a feeling he would feel in the morning. Luckily, his upper half with all the important bits made it onto the couch, but that didn't stop Gabe from gasping loudly and apologizing profusely.

"Are you all right?" he asked as Sam tried, and failed, to regain his balance.

"M' good," he slurred, the pain a dull ache in comparison to the sweet floating feeling of being drunk. For some reason it was _really_ hitting him now, "You got some more drinks up here?"

"Oh no, I think you've had enough alcohol," Gabe said firmly, smoothing his hair back from his flushed face. It felt cool, which was strange since Sam knew the man was very warm, "You stay here while I get you some water."

Sam grunted unhappily at the mention of water (why would he drink _water_ when he could have a shot of something better?) but stayed put as Gabe walked out of eyesight.

The vaulted ceiling above held his attention for a few brief moments, but the faint noises of traffic somewhere past his head had him sitting up and peering towards the far wall.

It took Sam a moment to process what he was looking at, but once his eyes and brain made the connection, he gaped at the sight before him.

Much of the wall was glass, with a set of barely-there doors in the middle that led out to a balcony. Past the balcony though was a great view of Lawrence, the glittering skyline bright against the night sky. The Fallen Angel must've been the tallest building in the immediate area for Gabe to have such an uninterrupted view, and Sam wondered if the man spent a lot of time looking out from this vantage point.

Standing took less effort than Sam expected, but the feeling of walking was more like floating as he approached the view, quite awestruck by what he saw. Even sober him would be impressed by the sight, but drunk Sam wanted more.

Luckily, the door was already unlocked (if it hadn't been Sam might've actually struggled with the lock), so all he had to do was push it open, letting in a slap of hot summer air and the sounds of the city.

"Nice," he breathed, stepping out onto the sizeable balcony and looking out. They must've been on the side the Fallen Angel because when Sam looked down, he didn't see the lit-up sign or herds of people. All he saw was a darkened street rising up towards him in a sudden wave of vertigo and double vision that had him clutching the railing.

Something pulled him back with such force that Sam's head whipped up to see a snatch of the light polluted sky. A glass shattered, and suddenly Sam was back inside Gabe's cool apartment, tugged backward by the man himself.

"Jesus _Christ_ , Sam, are you _trying_ to give me a heart attack?" the man demanded as he flicked on what sounded like a light switch.

The assault of light on Sam's eyes confirmed his initial thought, sending him swaying again with a groan as he struggled to acclimatize to the sudden change.

There was a colorful swear that would put Dean to shame before the lights dimmed and Sam could somewhat see again. He squinted against the spots in his eyes, struggling to put detail to the silhouette before him.

It was Gabe looking fairly apologetic and more than a little ruffled. Sam glanced back at the balcony to see a broken glass of water and looked back at Gabe with a frown.

"Sorry," he said, not quite understanding the situation, but feeling the need to apologize anyway.

Gabe sighed and shook his head, "It's fine, but what were you doing out there?"

Sam shrugged, rubbing his neck bashfully, "I wanted to see."

There was a moment's silence before Gabe reached for his hand, intertwining their fingers. Sam followed the man back out to the balcony, where they stood for a moment to look at the view.

"Don't let go of my hand. I don't want you tipping over again," Gabe said gruffly as a faint summer breeze passed over their heads. It wasn't enough to alleviate the heat, but it stirred the air enough for Sam to feel it.

Sam kissed him in response, a bit clumsy in his aim, but determined in his attempt. There was no back and forth for control this time, as both of them were content to let it be brief and sweet.

They stood there for an indeterminable amount of time before a sudden wave of fatigue overcame Sam. Gabe seemed to notice and led him back inside, tugging him past the wall with the TV and down a dark hallway to a door at the very end.

"Time for you to sleep," he said, leading Sam to the white sheets spread over a large bed that could be made out in the dark. Gabe didn't turn on the lights this time, which he was grateful for. He didn't think his eyes could handle it again.

"Why?" Sam asked, even as he flopped face down onto the bed, and Gabe snorted.

"You'll thank me in the morning," he responded as he began to tug off Sam's shoes.

The Winchester groaned unintelligibly before rolling over, just awake enough to be mindful of not kicking Gabe in the face. He was positive one of his feet was the size of Gabe's face, and kicking him wouldn't end well.

"Buttons," he said, fumbling at his shirt with clumsy hands, "Can't sleep with a shirt."

Cool air hit his socked feet, and he could hear the thump of his shoes fall to the floor.

"Shirt?" Gabe echoed, and Sam peered into the dark, barely making out the faint gold on Gabe's shirt. His eyes had adjusted enough to make out vague shapes, but not any details.

"Help me with it," he requested.

There was a long pause before fingers slid up his chest, the mattress sagging slightly as Gabe sat by his side. The baroque pattern felt nice against his skin as more and more of his chest was exposed, but Gabe himself didn't linger long with his touches.

Sam waited patiently as the buttons of his shirt were undone before pouncing, drawing a surprised gasp from Gabe as the Winchester rolled them to the side on a whim. The bed must've been very big because Sam didn't hit pillows or an edge at all.

"This is better," he said, wrapping his arms around Gabe and breathing in his now familiar scent.

"Sam," Gabe began to protest, but Sam only made an exaggerated hushing sound and pressed his face into the hollow of Gabe's neck, feeling the thin chain press against his cheek.

"We can just…sleep," he murmured, eyelids already growing heavy, "Kissing was nice, but this is better."

Gabe sighed before carding a hesitant hand through Sam's hair. Sam hummed contentedly, the floating feeling dissipating slightly now that he was grounded by Gabe. Pretty soon he'd be out like a light, and he almost was when Gabe spoke.

"This _is_ better," he murmured, voice sounding small in the dark, "Too bad this was all just to help you get revenge."

Gabe squirmed a bit, toeing off his shoes before running his hands down Sam's bare back. It took all of the Winchester's self-control to keep from shivering at the touch. He was almost asleep though, eyes now shut as he barely heard the last words.

"Maybe in the morning, I can convince you to stay."

 _There's no maybe about it,_ Sam thought before finally falling asleep.

…

Sam Winchester woke to the worst hangover he'd ever had in his life, and considering he'd partaken in a drinking contest with his dad and brother on his 21st, that was certainly saying something.

Pretty much everything hurt. His head pounded, his eyes burned, and for some reason, his lower back ached as if he'd hit it against something. The bed he was in was very soft and smelled clean, which meant that at the very least he hadn't done anything stupid like drunkenly hook up with someone.

He cracked open one eye experimentally, squinting at the filtered light coming in through the sheer white curtains. Something on the bed caught his eye though, and Sam stared at the familiar gold and black shirt crumpled on the pillow next to him. His shirt was next to it, looking plain compared to the baroque decorated fabric.

 _Gabe._

"Oh. Shit," he hissed, voice cracking. His mouth was dry and tasted strongly of stale alcohol.

"Shit, shit, shit," he repeated like a mantra as he scrambled to awareness. The previous night was a blur, but he could recall riding in a Lamborghini and drinking lots of strong drinks and kissing.

 _Kissing? Wait, was there more than kissing?_

Sam yanked back the sheets and sighed with relief when he saw he was still wearing pants. It seemed he'd passed out before he and Gabe had done anything more than make out.

He slumped, rubbing his face as he tried to collect his thoughts. Last night had been a roller coaster of events, but it was Gabe's words at the end, whispered in the dark, that stood out to him the most. He was surprised he even remembered them considering how shitfaced he'd gotten, but in the morning light they stood out in his head as if his brain made sure he would remember.

 _Maybe in the morning, I can convince you to stay._

Gabe _did_ like him. It was almost impossible to believe, but it was true. Sam knew what he heard, and besides, he didn't think he could just leave anyway. He liked the other man too much to walk away without a fight, but now that he knew Gabe reciprocated in some kind of way, it made it all the easier to stay.

With that sorted out, Sam fell back, slumping against the headboard. He could hear someone moving around, presumably Gabe, but he was perfectly content where he was for now, his realization making him smile.

 _He likes me, and I like him._

Sam turned his gaze to the side, where his phone sat on a nightstand, along with a glass of water and some aspirin.

He seized the pills first, draining the glass to finally rid himself of his dry mouth. Only then did he grab his phone, gaping as he saw not only the time (it was _long_ past noon) but the sheer amount of notifications.

"Damn," he said, turning down the brightness of his phone to spare his still sensitive eyes as he tried to make sense of where all this activity had come from.

There were texts and missed calls from various people, but it seemed Instagram was the source of all the hubbub. Opening the app revealed a whole slew of notifications, but it quickly became apparent on his feed what had started it all.

A picture of him and Gabe kissing at the bar had Sam staring for a solid minute. He had to admit, it was a good shot, even if it made him flush in embarrassment. It was clear that it was a very passionate kiss, as his fingers were entangled in Gabe's hair.

There were tens of thousands of likes and hundreds of comments to go with the original post (which had been posted from theoriginaltrickster) that seemed to start it all, but Sam was more focused on the caption.

 _He's always been a little shy, which is why this took so long, but he finally agreed to make his big debut tonight. Here's to you, Sam._

It was short, but for some reason, it made Sam's heart do a funny leap in his chest.

Now all the DMs and texts made sense. It must've been all his friends trying to figure out what the hell was going on, and Sam shook his head before going to his texts and pulling up one person in particular.

Dean had called him five times and texted him twice, both of the texts somehow summing up his brother's personality.

 _Dean: I'm going to be Charlie's backup when we fight that bitch. Are you OK? I can make some burgers if you want, just get back here._

 _Dean: I just saw the IG post. I have no idea what's going on, but I've got your 6. Call me ASAP._

Sam smiled before firing off a quick text to let Dean know he was all right and that he'd call him later. He then went through the rest of his messages, which ranged from shock and confusion to glee that he'd finally gotten over Jess and excitement that he was dating the Trickster. Charlie was ecstatic he'd finally acknowledged that he was bi and Kevin had asked him if the nightclub's bars were _really_ inlaid with gold. He had gained hundreds of followers overnight and gotten dozens of DMs from random people asking invasive questions. Everyone was trying to figure out what was going on, and it seemed, who exactly _he_ was to have attracted the attention of the Trickster himself.

"Just a guy that wanted revenge," he muttered to himself, setting his phone to the side. He'd deal with all that later, but right now, he needed to get up before he didn't get up at all.

Standing up sent a tell-tale lurch through his stomach, and Sam groaned before making a beeline towards the bathroom.

After what felt like an eternity of puking up his guts, the now humbled Winchester flushed the toilet and got up on shaky legs. He wasn't sure what he'd drunk last night, but whatever it was, he was staying far, _far_ away from it.

"Oh good. You're awake."

"Holy shit!" Sam exclaimed, nearly stumbling backward into the shower behind him at the sound of the deep, unfamiliar voice.

A cool hand caught him before he could crash into the frosted glass door behind him, tugging him upright before letting go quickly. The voice belonged to a man a few inches shorter than him, with piercing blue eyes, a white button-down tucked into black slacks, and a loosened blue tie.

"You're doing well considering you supposedly had six of Balthazar's Unicorn shots," the man said, as if he hadn't just appeared out of nowhere and spooked Sam, "Gabe made it sound like you had alcohol poisoning, and frankly I'm amazed you don't have it."

"I, uh-wait, who _are_ you? And Unicorn shots?" Sam asked, growing more and more confused by the second as the stranger peered critically into the toilet.

"I am Castiel, Gabe's cousin and unofficial family physician," he said, frowning momentarily before opening a drawer, "Unicorn shots are a potent alcohol concoction that Balthazar is disgustingly proud of. The record anyone has drunk consecutively is four, which is why I assume Gabe was convinced you needed a hospital."

Sam frowned as Castiel pulled out a toothbrush still in the package and handed it to him, accepting distractedly as he looked at the toilet.

"Is _that_ why my puke was iridescent?" he asked, part horrified, and part grudgingly impressed with Gabe's crazy cousin.

Castiel's lips quirked, "Yes, I'm afraid so. All things considered, you're doing very well. You must process alcohol very well to be upright after the night you had."

"Winchesters are good at handling alcohol," Sam muttered before running a hand through his hair, "What do you mean by 'unofficial family physician'?"

At this, Castiel toed the floor, fiddling with his shirt cuffs.

"I am…still in medical school, so I am not an official doctor," he admitted, "However, I have learned enough that Gabe calls me at times when someone has partaken in too much at the nightclub."

"Oh," Sam said (how many cousins did Gabe _have_?), "And how often you do you do that?"

"Too much," Castiel grumbled petulantly before shaking his head, "As you don't seem to require any serious medical assistance, I recommend taking a shower and eating a good breakfast to help with the hangover and lots of water of course. I'll inform Gabe you're awake so that he can stop pacing the kitchen and make me dizzy with his fretting."

"You don't think Gabe would mind me taking a shower?" Sam blurted out as Castiel walked out of the bathroom.

The blue-eyed man paused in the doorway, turning back with a faint smile on his face. Sam had a feeling it was the serious man's equivalent of a grin.

"Gabe is a very private man despite the lifestyle he leads," he said, "I believe the fact that he exposed himself in such a public manner with you says it all."

With that, Castiel stepped out, leaving Sam holding a toothbrush and feeling quite disoriented in the bathroom, and the hangover had nothing to do with it.

He did as the man said though and took a _very_ hot shower. His skin felt as if he was getting pinpricked a thousand times over at first, but the oversensitivity wore off soon enough, and Sam stepped out feeling a lot better. Brushing his teeth twice helped even more, and he almost felt human by the time he finished his ablutions.

The only problem was that his pants had gone missing.

"What the hell?" he muttered, looking around in vain for the missing garments. They were nowhere in sight, and Sam sighed before wrapping a towel around his waist and stepping out into Gabe's bedroom.

Everything had been straightened out, and Sam looked around at the mostly white room curiously before reminding himself what he was looking.

A quick search of Gabe's room proved fruitless, and Sam sighed before deciding to brave the living room. He wanted his clothes more than he cared about any potential embarrassment that would come from coming out half naked.

"Gabe? Do you have my clothes?" he called out, hearing muffled voices from ahead.

"…give them _back_! Honestly Balthazar…"

"…just helping you out…"

Sam stepped out into the living room and looked to his left, where an open kitchen stood. He must've been really drunk to have missed it last night because it was right by the elevator. Gabe and Balthazar (who was still wearing the ridiculous leather pants) were wrestling back and forth with what suspiciously looked like his clothes. Castiel was sitting at the large marble island, watching them fight dispassionately as he ate.

"Are they like this all the time?" Sam asked as he approached.

Gabe and Balthazar snapped to attention as Castiel nodded tiredly and gulped down his coffee.

"Aren't you glad I stole his clothes now, Gabe!" Balthazar crowed with a wolf whistle that had Sam flushing.

"Shut. Up," Gabe growled, taking advantage of his cousin's distracted state and snatching the clothes back. Sam was pleased to find that his face was quickly turning pink, "You're a menace to society! Out, get out!"

"But _Gabe_ ," Balthazar whined, "I took the pictures for you!"

"And then pumped him full of Unicorn shots. Why I even let you serve them is a mystery!" Gabe exclaimed, throwing his hands into the air. Sam had the idle thought that if his shirt had been white, it would've been tossed about like a surrender flag.

"Because they're pretty in the glasses?" Balthazar suggested coyly.

Castiel sighed as Gabe stared at Balthazar for a long moment before launching himself at the leather-clad man. Sam jumped slightly as they crashed to the floor out of sight, but Castiel didn't seem too concerned as he continued to eat.

"They'll be done soon. Here, sit," he said, gesturing to one of the bar stools, "How are you feeling?"

"Um, confused but alright," Sam responded, eyes entranced by the sheer variety of food before him, "Do they always…"

"Yes," Castiel replied simply, "They have a tumultuous relationship, but it comes from their shared wild personalities. One of them on their own is enough of a headache; both of them together is beyond words."

"Huh," Sam grunted as he began to load a plate, "Crazy enough to start a business together?"

Castiel eyed him curiously over the rim of his coffee mug.

"You're a perceptive man, Sam," he said bluntly, "It was an idea born from a family reunion two years or so back. Everyone was drunk, and we're still not sure who had the original thought, but Gabe and Balthazar were hooked on the idea. And the two of them working together…"

He drained his mug and set it down with a sharp thud, "Well, it's no surprise they launched themselves to success. Behind their extravagant personalities and hare-brained tendencies, they're remarkably sharp and cunning."

Sam watched as Castiel stood and stooped down to haul Balthazar up by his collar, brushing down his shirt absently before dragging him towards the elevator.

"It was good to meet you, Sam, even if I'm still not quite sure who you are," Castiel said as the doors slid open, "Stop _squirming_ so much, Balthazar."

"Whatever," the man scowled before winking cheekily at Sam and waving, "Bye Sam! You took those Unicorn shots like a champ!"

The doors shut on the pair, leaving Sam alone with a much more disheveled looking Gabe and enough food for a small army.

"Well, _that_ was enlightening," the Winchester remarked as he began to eat.

Gabe ran a hand through his hair and winced, "Yeah, they're… _different_."

Sam snorted, holding out a hand which Gabe stared at questioningly.

"My pants, please," Sam said innocently.

"Oh! Right, uh, pants," Gabe said, pink again as he handed over the poor clothes.

Sam stood, unwrapping the towel and letting it fall to the floor. The counter was just barely level with his hips, which meant he was pulling the ultimate tease on Gabe.

He had to give Gabe credit; the man showed very little reaction besides a faint choked sound. His eyes gave him away though, but Sam tried not to let the darkened irises affect his little game as he pulled on his pants.

"So, I think Plan A has gone pretty well," he remarked casually as he zipped up his fly, "I haven't heard a peep from Jess, and everyone seems convinced we're dating."

Gabe swallowed, his eyes linger on Sam's hands before his eyes returned to his face.

"Well, I think Jess not contacting you is on me," he admitted, a contrite look appearing on his face.

Sam arched a questioning eyebrow, and Gabe shrugged, crossing his arms defensively.

"I woke up to your phone ringing. It was her, and she was pretty pissed, so I got pissed back," he said sheepishly, "Needless to say, I'm pretty sure she got the message."

 _Gabe told Jess off for me, and_ succeeded _? Not even Dean managed that._

"I _slept_ through that?" Sam asked incredulously, and Gabe nodded.

"That's why I, uh, initially called Cas. Your ex has a pair of lungs, that's for sure."

"Yeah," the Winchester agreed distractedly before walking around the counter and scooping Gabe up in a hug that took him off his feet.

"Thanks for that," he said gratefully. While many people had had words with Jess on his behalf, he'd never truly snapped on her himself, and he was glad Gabe had cared enough to take the initiative.

"No problem, Sam," Gabe responded, his voice muffled from where his face was buried in his chest, "Listen, about last night…"

Sam bit his lip nervously. He'd heard what Gabe said (he didn't think he'd ever forget it), but what if the man had changed his mind?

 _I don't want to go though._

"I'm really sorry about the whole drinking thing," Gabe began, stepping away with a worried look on his face, "Balthazar always gets overenthusiastic when someone with a good liver comes in, but I really should've put a stop to it, and-"

Sam stared at the rambling man for a moment before rolling his eyes and cutting him off with a toe-curling kiss.

"Is that all?" he asked with amusement as they broke apart for breath, "I thought you were going to kick me out or something."

Gabe looked pleased about the kiss before frowning.

"Why would I do that? Plan A is still in effect!"

"Oh really?" Sam asked curiously, and Gabe nodded fervently, toying with his collarbone. With a faint flush on his cheeks and his bright eyes, he made for a picture just as pretty as he was last night.

"You see, now that we're public, we have to continue on," he said, golden eyes glinting, "Otherwise it'll be clear to Jess that we're just pretending, and the revenge will be ruined."

Sam caught on quickly, smiling indulgently as he twirled the man towards the kitchen island and set him on top of the kitchen island. Gabe slung his arms around his neck, fingers tangling in his hair.

"You make a good point," he murmured, cupping the side of Gabe's face, "I think Plan A was always meant to be a long-term plan, wasn't it?"

He was going out on a limb here, but his risk paid off as Gabe smirked his trademark Trickster smirk.

"I _did_ tell you I recommended Plan A," he said smugly, crossing his ankles at the small of Sam's back.

"Hmmm, how _ingenious_ ," Sam said as he leaned in a fraction. He now realized what Castiel meant when he had said that Gabe was smarter than he let on, "You wanted in my pants the moment you sat down across from me, didn't you?"

"One way or another, I was going to have you," Gabe said boldly, "Plan A was one of my cleverer moments, and you not knowing, or _caring_ , who I was made it even better. Dishing out karma and seducing you, all in one!"

Sam couldn't even bring himself to mind that Gabe had come up with a two-fold plan to seduce him. Gabe had genuine intentions at heart, and it lined up perfectly with what he wanted anyway.

"You're lucky I like you," he said, earning himself a bright grin from Gabe, who seemed to have been a little nervous about how he would react to his admission.

"I'm _very_ lucky indeed. Care to experience just how much I like _you_?" he asked slyly.

Sam grinned cheekily, "Would that be the seduction bit of Plan A?"

"Oh shut up!" Gabe exclaimed, shoving him playfully.

"Make me," Sam dared.

Gabe's eyes became intense as he tilted his head and smiled. Sam had a brief moment to recognize it as the very same look Gabe had worn when he'd first introduced himself before the Trickster leaned in and did just as Sam asked.

* * *

 **AUTHOR'S NOTE**

Hello readers! This is one out of two oneshots that I worked on when I was stuck on Chromaticity, but ironically enough, this wasn't the one I thought I'd finish first. However, I got more and more into it, so here it is. Originally inspired by a gorgeous baroque shirt I saw on the Internet and combined with a Tumblr prompt I saw ages ago, I present this trainwreck of a oneshot.

I don't want to skew the word count, so I'll cut the author's note here. If you want to know a little more of the process behind this story, head over to AO3, where my full Author's Note will be. For those interested in what's going on with Chromaticity, I am working on the promised Gabe oneshot, and that will go up before I begin the sequel.

Final Word Count: 14,607


End file.
